Acetyl chloride → N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amine

HRID 1612274Notes

Reaction equation

HRID 1612274 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:26][CH3:27])[C:12]([NH:17][C@H:18]2[C@@H:22]([O:23][CH2:24][CH3:25])[CH2:21][NH:20][CH2:19]2)=[N:13][C:14]=1[CH2:15][CH3:16].[C:28](Cl)(=[O:30])[CH3:29].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:28]([N:20]1[CH2:21][C@H:22]([O:23][CH2:24][CH3:25])[C@H:18]([NH:17][C:12]2[C:11]([CH2:26][CH3:27])=[N:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:14]([CH2:15][CH3:16])[N:13]=2)[CH2:19]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 103098205-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine

Product 1

HCID 58583258N-[(cis)-1-acetyl-4-ethoxypyrrolidin-3-yl]-5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-amineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2,4-dichlorophenyl)-N-[(cis)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine (105 mg) in methylene chloride (5 ml) under N2 was added acetyl chloride (0.027 ml). The reaction mixture stirred for 30 min and was poured into saturated sodium bicarbonate (20 ml), extracted methylene chloride (2×20 ml), dried MgSO4, filtered and concentrated. MPLC chromatography was run on a biotage 25 S column with 60% ethyl acetate/heptane to provide the title compound as an oil (79 mg, 69%): 1H NMR (400 MHz, CDCl3) δ) 7.50, 7.34-7.26, 5.30, 5.12, 4.81, 4.19, 4.01, 3.87-3.67, 3.61-3.37, 2.72, 2.48, 1.33-1.26, 1.14; HRMS (FAB) calcd for C22H28Cl2N4O2+H 451.1667, found 451.1667.

Workup

  1. extractionextracted methylene chloride (2×20 ml), dried MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-785ce332d0104d88af5fea7c59c7c73f
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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